Linger
by wherethelightis
Summary: Okay, it's been done a million times before... but not by me! Jess has lived in Stars Hollow all his life, and he and Rory have always been best friends.
1. Prologue

**author's note:** Welcome! I just had to get into the Jess-and-Rory-knew-each-other-as-kids type of story… so here's my take on it. Hope you enjoy.

**disclaimer: **Once, I actually had this dream where I was going to meet Milo Ventimiglia, but then all of these horrible things happened and I didn't get to. It was devastating. If I own him and Gilmore Girls, that obviously wouldn't have happened.

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**prologue**

"Come on, Jess, put the stools back," a frazzled looking Luke told a small, curly haired boy sitting in front the cash register. His short legs were dangling, feet from the ground.

"What's he up to now?" Lorelai walked into the diner, a three-year-old Rory swinging on her hand.

"He has single-handedly moved all of the _customer's_ stools from the front of the counter to behind it," Luke sighed, rolling his eyes slightly.

"Yeah, so I can serve people! See? I jump back and forth from one to another. 'Cause otherwise I wouldn't be able to see anyone!" a proud Jess exclaimed, demonstrating.

"Ooh, serve me, Jess!" Rory said, clapping her hands together excitedly.

"But Jess, Rory has nowhere to sit, because _you_ put all of the stools back here," Luke pointed out.

"Oh." Jess rested his head in his hands, contemplating. Then he jumped off of his stool. "You can have that one over there. I don't really need it." He attempted to push the end stool around the counter, but struggled because of the stool's size advantage over him. So Lorelai took it from him, placed it in front of the counter, and plopped Rory on top.

Jess wiggled up onto his own stool, behind the counter. "What can I get you, miss?" he asked Rory, completely seriously.

"Coffee!" Rory replied, wiggling her feet around.

"Corruption," Luke muttered.

Lorelai just beamed and ruffled Jess's hair. "So, buddy, you've got a birthday coming up next week, right? The big oh-four?"

Jess nodded, still serious. "Yup."

"What are you asking for?" Lorelai prodded.

"A bike –" he looked pointedly at Luke – "and some new books." This time he looked at Rory.

"More coffee, please!" Rory held out her cup and made her best fawn face for Jess.

"Corruption," Luke muttered again.

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seven years later 

"Rory… I have something I need to tell you." Rory and Jess were lying on the couch in the apartment above the diner, Jess's arm casually draped over Rory's shoulders.

Rory turned to look at him, a concerned look on her face. "Yeah?"

"My… my dad… called here on Monday," he said, his chocolate eyes containing none of the spark they had just a few minutes ago.

"Did you… did you talk to him?" Rory linked her fingers through his. She knew this was tough for him. Jess's father had never called before, and Jess couldn't even remember what Jimmy Mariano looked like. But Rory knew that Jess wanted to forget.

"No… I'm not even supposed to know. I came home and I heard Luke on the phone, yelling at him, telling him never to call again."

"Oh, Jess…" Rory wrapped her arms around his torso in a sort of half-hug. "I'm so sorry."

"It's okay," he said, shrugging slightly, "I'm just glad Luke was home and I wasn't."

"Yeah," Rory agreed. "Just remember, you'll always have me.

"And you'll always have me," he replied, reciprocating her hug, the fiery spark returning to his eyes.

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Rory would always remember the first time she caught him. They were fourteen, just finishing up the eighth grade. She went down to the bridge to find him, and he was just been sitting there. Smoking. He turned his eyes toward her and she looked away, praying that her eyes were deceiving her. But when she looked back again, he was still there, putting the cigarette up to his mouth. So she ran. She didn't know what hurt most: the fact that he was smoking, or that he didn't follow her.

The worst part was, she had been warned. Lorelai had told her countless times that Jess had changed, he wasn't a good kid anymore, that he stole and drank and smoked.

But Rory had refused to believe it. Jess wouldn't do that, she had told her mother, which only wound up escalating into a fight in which both Gilmore girls had stormed off to their rooms and slammed their doors.

And now, Lorelai was right. Rory fell onto her bed, burying her head in her hands. Jess wasn't a good kid anymore.

When Rory awoke two days later on Saturday, much later than normal because of the late-night movie night she and her mother had had, to the sound of two people in a heated argument. She could make out a few words: hurt… can't… Rory…

It was her mother and Jess, arguing about her. Rory buried her head under her pillow, blocking out the shouting.

Then she heard the front door slam, and her mother stomping up the stairs to her room. Rory ran to her window and saw Jess walking away casually, lighting up a cigarette. She shut the blinds quickly.

Ever since Rory had come home from the bridge two days before, Lorelai had known something was wrong. Rory had refused to talk to her, but Lorelai had put two and two together. She knew it was Jess.

Lorelai was in the kitchen when Rory burst out of her room, pulling a sweater, shoe, and hat on all at the same time.

"What's going on?" Lorelai asked.

"I'll talk to you later!" Rory called, already out the front door and running full speed down the steps.

When Rory arrived at the bridge five minutes later, Jess was sitting there smoking, his legs dangling above the water, just as she had known he would be.

She marched onto the bridge, grabbed the cigarette out of his mouth, and threw it into the water.

"Hey!" he exclaimed, "Those are expensive!"

"What the hell is going on with you?" she demanded, her hands placed haughtily on her hips, her eyes narrowed to slits. Without waiting for him to answer, she spoke again. "You smoke, you drink, you steal… did I miss anything?"

"Rory…"

"Do you gamble, perhaps?"

"Rory…" Jess tried again.

"Oh, maybe you pick girls up off the corner in Hartford. What about that?"

"Rory!"

"What?" she looked irritated at being interrupted in the middle of a rant.

"I went to see my dad."

"Jess! That's not something you can just _joke_ about!"

"I'm not joking, Rory!"

"Jess, come on. What's really going on?"

"That _is_ what's really going on! I went to see my dad!" he shouted, completely pissed at her for being so god damn _dense_.

This seemed to make Rory come out of her ranting state. "What? When?" She sat down on the bridge.

"When you and your mom took your road trip and Luke was at his conference in New York." He sat next to her.

"That's why you didn't want to come with us," she realized. "So… you've been holding all of this in for… months?"

He nodded.

"Jeez, Jess…" her voice lowered to barely a whisper. "What happened?"

He shrugged, his hands in his pockets and his eyes lifeless. "I went, and… he was so stoned he didn't know who I was."

"Oh, Jess," Rory put her arm around his waist. "You could have told me… you didn't have to start… this!" She waved her arms around vaguely, but he knew what she meant. The smoking and the drinking and the stealing.

"Don't you understand, Rory?" His voice was raising and he shoved away from her, standing up. "It doesn't matter how many fucking people I tell, because that doesn't change the fact that my own fucking father doesn't recognize his own son, does it?"

"Jess, I –" Rory began, but he cut her off.

"No, Rory, don't even start! I'm sick of your pity talks! Yours, and Luke's, and your mom's – everyone's!"

"I'm –"

"You say you understand, but you can't _honestly_ know how this feels! Yeah, your dad isn't around much, but at least he might maybe, just maybe, recognize you if he bumped into you on the street! At least he calls now and again, and remembers your birthday! And at least you live with your fucking mother! Do _not_ tell me you understand, because you _don't_, okay? No one does!"

Rory stood up, tears welling in her eyes. "You're right. I guess I don't understand," she said, before turning her back and walking away, not looking over her shoulder once.

The fight was the worst one they'd ever had. Rory refused to talk to Lorelai about it, because she knew that there would be no way to regain Jess's trust if she told her mother that he had snuck out to see his father.

Unfortunately, this also meant that there was no way for Rory to help Lorelai understand why Jess had been acting so messed up lately.

Rory was even afraid to tell Lane about the fight, and Lane was her second-best friend – after Jess, of course.

After two weeks of avoiding Luke's (a very difficult talks, involving doing lots of pretend studying and developing a sudden obsession with Al's Pancake World), Rory steeled herself and went in. Her morale perked up when she realized that Jess wasn't even there, and then dropped again when she remembered that she _really_ need to talk to him and end this thing already.

But right as her coffee arrived, Jess walked down from the apartment. He stiffened ever-so-slightly when he noticed her (something that only someone who knew him as well as she did would recognize), but he walked up to her nonetheless.

"Hey," he said, not quite looking her in the eyes.

"Hey." Her grip on her coffee mug tightened.

They stayed like that for what seemed like ages, not quite looking at each other. A thick silence hung over them. Rory sipped her coffee, unable to meet his eyes.

Finally, Jess spoke. "You want some more coffee?" he asked, gesturing at her empty mug.

"Sure," she answered, sliding it toward him.

He took her mug into the back room, and when he returned, handed it to her with a napkin, saying, "Enjoy" before ringing up a customer at the cash register.

Rory dabbed at her mouth with the napkin when something caught her eye. She unfolded it and saw Jess's scrawled handwriting. _I'm sorry._

She grabbed a marker off the jar on the counter and wrote back. _Me too._

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So, there's chappie one! I hope you liked it. Don't worry, there won't be this much drama in every chapter. I just never like how in other stories like this, it's never explained how or why Jess went "bad," so this is my explanation. There also won't always be this much swearing.

Anyway, next chapter we get to Rory and Jess when they're seventeen.

Remember, reviews equal love, people.


	2. Sweet Sixteen

**author's note. **Okay, I lied. This is going to pick up where the first season starts… so Rory and Jess are sixteen, not seventeen.

Also, thanks _so_ much for the overwhelmingly wonderful responses! I wasn't expecting anything so great for just the first chapter… keep it up, please! They really helped me get this chapter up so, _so_ much faster than it would have been otherwise.

**disclaimer. ** I have a question. Does anyone actually believe that I own Gilmore Girls?

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"Come on, Rory. It's your sixteenth birthday we're talking about here. You can't just shrug it off. You know, 'Sweet Sixteen' and all that cheesy stuff?"

Rory picked up a can of soup off of the shelf. "Wow, I didn't picture you as a 'Sweet Sixteen' type of guy."

Jess shrugged. "Well, you know what they say. You learn something new every day."

"I guess so. My mom has been talking a lot about what to do for my party – you should probably talk to her."

"Yeah, and get my head cut off? No, thanks."

"Jess, come on. She doesn't hate you _that_ much."

"I beg to differ. She hasn't spoken one nice word to me in three years."

"She wants to like you, really…"

Jess just scoffed.

"No, really, she's just… well… my mom. So she always puts me first, so when she found out you were doing some stuff that… that she didn't want me doing, she freaked out. She thought I would start, too."

"But you didn't, and she still hates me."

Rory couldn't help but nod. It was true; Jess was not exactly Lorelai's favorite person in the world. "Oh, I need some vegetable oil. I'll be right back. Here, take these and get in line." She piled a couple of cans into Jess's arms.

"Vegetable oil? And you guys cook… when?"

"It's not for us, silly. It's for when Cinnamon gets stuck under Babette's porch, remember?" Rory rolled her eyes at him.

"Of course. How could I forget?"

She walked two aisles over and turned in, walking straight into someone. They dropped the few cans they had been holding.

"Oh, my gosh, I'm so sorry." Rory said as she bent down to pick up the cans.

"No, I got it," a male voice said, reaching for the same can that Rory was. Their hands brushed slightly and she looked up.

Standing up, he said, "I'm Dean."

He was tall, taller than Jess, she noted, and she had to look up to meet his eyes. "Rory," she said. She guessed from the Doose's smock that he was wearing that he worked there.

"Yeah, I know."

When she looked at him questioningly, he said, "I've just seen you around, that's all. You're famous around here."

She blushed and looked down. "It's nothing really… these people are just crazy. Did you just move here?"

"Yeah. From Chicago. You go to Stars Hollow High, then?"

Rory felt an arm slide around her waist, and she looked over to see Jess.

"Nah, our girl's too smart for Stars Hollow. She has to travel all the way to _Chilton_," Jess said.

Dean looked from Rory to Jess. "Boyfriend?" he asked.

"No!" Rory said, a bit too hurriedly. "Um, no. Just friends."

Jess smirked at her, while Dean just said, "Oh."

"Yeah, well, we'd better get going… busy day at the diner, and all…" she trailed off. "Anyway, see you around."

The whole time she was paying, Jess continued to smirk at her. When they got outside, she turned to him. "What?"

He put on an innocent face. "'What' what?"

She rolled her eyes. "You know what, Jess."

"Oh, it's nothing. You were just pretty quick to say that I'm not your boyfriend."

"Well, excuse me if I'm wrong, but you're not!"

"Okay. Why do you like him so much, then?" They had resumed walking.

"I don't! I just met him," Rory defended.

"Quick again. We've really got to work on that. It makes you look pretty guilty," Jess teased.

"Apparently not, since you're _not_ my boyfriend and I _don't_ like him. Why do you hate him so much?"

"I don't," he replied coolly.

"Yeah, right. You're a worse liar than I am."

"I don't know… he just has a bad vibe about him," Jess shrugged.

"Perhaps it's just the 'city vibe'?" Rory asked. "He is from Chicago."

"Nah, it's not that. Forget it. It's not important. Listen, I promised Luke I'd help with the lunch rush – I'll meet up with you later." And with that, he handed her her bags and walked toward the diner.

"And I _don't_ want a party!" she called after him.

He threw his hands up in the air, never turning around. "Fine!" he shouted.

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The next day, Rory walked into the apartment above Luke's after school to find Jess with a black eye and wrapped arm.

"Oh, my god, Jess, what happened?" She ran over to him.

Jess just shrugged it off. "That friend of yours thought it would be fun to pick a fight."

"You were in a _fight_? Who's 'that friend'?" Jess didn't have a perfect record, but he had promised Rory he would try to be at least a bit less… temperamental.

"Listen, Rory, it's really not a big deal. A few blows were launched, insults shouted, and then someone came and broke it up."

"What do you mean, it wasn't a big deal? You have a black eye and an injured arm, Jess! That's not _nothing_! And who was it with?"

"That guy from Doose's. Dean, was it?"

"_Dean_? You got in a fight with _Dean_? Jess! He's new here, and you just had to get into a fight with him? Prove that it's your turf, or some stupid guy thing? Is that it?" Now she was getting mad. Jess had _promised_ her that he would try to be better, and this sure didn't look like trying to Rory.

"Why do you automatically assume that _I_ started it? Because, for your information, I didn't! That jerk did!"

Rory raised her eyebrows. She realized that she was being a little ridiculous; she should have given Jess at least a little say in the matter. But really, this was unbelievable. "Really? What was it about, then? What was such a big deal that you couldn't just suck it up and walk away?"

"You know what, Rory? I don't have to discuss this with you. This is none of your business."

"Fine!" she shouted, leaving the apartment and slamming the door as hard as she could behind her.

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"How was Nazi school, babe?" Lorelai greeted Rory with a kiss on her forehead.

"Fine," Rory lied, hugging her mother briefly before going to throw her backpack on her bed.

"A boy called for you," Lorelai shouted from the kitchen.

"Jess?" Rory called, hopeful. Besides, what other boy did she know well enough for him to call?

"No," Lorelai replied, "A 'Dean.'"

_Dean_ had called? _Dean_?

"Oh," Rory said, walking into the kitchen. She tried to play it off like it was nothing special. "Did he leave a number?"

"Yeah. It's by the phone." Lorelai, however, didn't seem to buy into Rory's act (she had always been a terrible actress, something she regretted at that moment). "So, who's this Dean guy?" Lorelai asked with a little too much glee for Rory's comfort.

"No one special." Rory shrugged. "I don't even really know him."

"Huh. Where do you know him from?"

Rory knew that the best thing to do was just to tell her mother – Lorelai Gilmore was bound to figure it out sooner or later. "He works at Doose's. Jess and I ran into him there yesterday. He just moved here… he's probably just looking for someone to show him around town or… something," Rory muttered lamely.

"Honey, it takes eight minutes to know your way around Stars Hollow. If he's already got a job, I bet he can already get around fine by himself."

But Rory had already grabbed the piece of paper with Dean's number and the phone and gone into her room, desperate to escape Lorelai's questions. "I've got homework!"

Instead of doing homework, however, she dialed Dean's number.

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Dean had asked her out to get coffee. _Dean_ had asked _her_ out to get coffee.

He had told her that he would call back the next day, once he knew of his definite work schedule for the next week. But the next day, he never called. Or the next. Rory tried to shrug it off – after all, he was just a guy. Maybe someone had died, and he had had to immediately fly cross-country. But she still couldn't make herself go into Doose's to face him, because in the end she knew that he had blown her off.

The next day, however – that is, three days after the original call – all thoughts of Dean were promptly driven out of Rory's mind, when she awoke to her mother sitting on the edge of her bed, staring at her.

"Mom! What are you doing?"

"Seeing how long it would take you to notice that I'm here," Lorelai answered. "So, now that you're up… get up! We have a busy day today, Miss _BIRTHDAY GIRL_!" She hugged Rory.

"Really? I don't remember us having any plans. I thought we were going to spend the day at home with some movies," Rory said, puzzled.

"Yeah, well, plans change," Lorelai replied, "So, up! We're going to hit Elena's Salon, then stop by Sookie's for this _amazing_ lunch I hear she has planned for you, do some shopping, and then head home for take out and a movie night! How does that sound?"

"That sounds _great_, Mom! Thank you so much!"

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"My feet are _so_ sore," Rory moaned, dragging her piles of bags on the ground behind her.

"Man… I should have booked Elena's for _after_ the shopping, so we could get foot massages and pedicures to sooth our mangled feet," Lorelai said.

Rory nodded in agreement. "Well, at least we'll be home soon for our movie night, during which we can lie on the couch and pig out."

"You are so my daughter."

However, Rory's plans of relaxation were thwarted when she opened the door to a seemingly empty house… only for her to jump five feet into the air when "_SURPRISE_!" was shouted at her from every corner.

People suddenly appeared out of nowhere, all talking and laughing and walking up to her all at once. Streamers hung from every square inch of her house, complimented by tulle and confetti and ribbons everywhere.

"Happy Sweet Sixteen," a voice said from behind her, their breath tickling her neck.

"Jess!" Rory squealed, "Did you do all of this?"

"Well," he shrugged, "with help from your dearest mother, of course."

Rory's jaw dropped. "You're kidding me. You actually collaborated with my mother? All for me?"

"All for you, birthday girl." He grinned. "I'm sorry."

She grinned back, throwing her arms around him and squeezing him as tight as she could. "Already forgotten. This is amazing," she said when she finally let go, "Thank you so much."

"I'm glad you like it. Oh, listen, Sookie's set up a whole huge buffet. You want to come check it out?"

"Sure," Rory answered, still awestruck. Jess had done this all for her. He had worked with her mom, which had probably made it a living hell for him, but he had done it anyway. Added to the fact that she knew that he absolutely loathed anything remotely resembling a decoration… it was incredible.

"Wow, this food looks great!" Rory exclaimed, grabbing a plate and piling it up.

"I'm going to go grab a soda. You want something?" Jess asked her.

"Sure… whatever's there. Thanks." Jess headed out onto the porch.

"Hey," a voice said from behind her.

Rory spun around and saw Dean. "Oh… hey."

"Look, I'm really sorry I didn't call you. It's just that when I was talking to Jess about the party, we both thought it would be better if I just lay low for a few days, so I didn't let anything slip. But I'm really sorry if you thought I blew you off or something." He looked truly sympathetic.

"Wait a minute. _Jess_ invited you? The same Jess you got into a fight with?"

Dean fidgeted slightly. "Yeah, the one and only. So… can we still get coffee sometime?"

"Oh, of course." Rory smiled. "Definitely."

Jess walked back inside, looking for Rory. He saw her talking to Dean, and before she could notice him, he had snuck off to the living room. After all he had done the last few days, it was the least he could do.

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**author's note.**

1. I realize that I've only written from Rory's point of view except for that last paragraph at the end – that's just been how it's worked out. Let me know whether you want Jess's point of view too, or if it's good with just Rory.

2. I know it seems like Rory and Jess always fight, but don't worry. It won't always be like that. I'm still setting the stage for things that will happen later.

3. I don't like writing bits with Lorelai in them. I think that they do such a great job with her in the show that anything I wrote would just be mediocre. But I still want to get the right balance here, so once again, let me know.


	3. Insectisyde on a Flagpole

**author's note.** Sorry for being _way_ late on this, but thanks for all your fabulous reviews!

Many of you have said that you want to see less of Rory and Jess fighting, so I've decided to add a complete chapter just for them to be nice! There isn't really that much actual plot in here, but I thought it would be fun. Also, I hope this sums up any questions as to why Jess invited Dean to Rory's party. If you are still unsure of something, tell me, pretty, pretty please.

I've also noticed that the previous two chapters have consisted of mostly dialogue. I didn't do that intentionally, but I guess it worked out that way just because that's the way the show is done. Do you guys like it that way, or would you like less?

I'm going to try to write more Jess, because tons of you asked for it, but it's turning out to be more difficult than I had expected because I don't want him to seem too sappy or OOC. So please, please, _please_ let me know if you like the small amount I put in here.

And lastly, to answer a question of few of you had, this _will_ be Rory/Jess. Although I can't guarantee it will be a smooth journey there.

Oh! One more thing: I just posted a Jess Season 2 oneshot… I would love it if you would check it out!

**disclaimer. **That's cute.

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_When one door of happiness closes, another opens; but often we look so long at the closed door that we do not see the one which has been opened for us._

-**Helen Keller**

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"So, where's your mom tonight?" Jess was shoving a filter into the coffee machine in the apartment above the diner. Rory sat at the table, nonchalantly flicking through the newspaper, not reading anything.

"There a huge function at the Inn tonight… the Baorin Bastell Concert Orchestra is in from Michigan, and apparently they're a _very_ demanding group." Rory rolled her eyes and blew a piece of hair out of her face.

"More so than the Obericott Oboist Elites?" Jess raised an eyebrow.

"Oh, way more. They won't even eat on plates that were made in China, because apparently, Michael Kuchta, this really famous composer, used to work in a sweatshop in China before discovering his hidden talent."

Jess scoffed. "If he's so famous, why've I never heard of him?"

"Um, maybe because you have never even managed to listen to _one_ classical song in your entire life." Rory rolled her eyes.

"That is _not_ true. Remember that time when there was an orchestra performance right in the center of town? I went to that." Jess crossed his arms over his chest defiantly and leaned against the counter.

"Yeah, and you sat through forty-five seconds before taking off."

Jess thought for a moment. "Huh. You're right. I take it back."

"Ha. And where's Luke all weekend?" Rory rolled up the newspaper and attempted to throw it into the recycling bin - missing terribly, of course.

"Some 'Business Management' conference in New York." Jess picked up the paper and put it in the bin.

"Really? I thought he swore never to go to another one of those again," Rory said.

"Yeah, well, it is our good ol' indecisive Luke."

"Very true."

Just then, Rory's phone rang from the other end of the apartment. She ran to get it while Jess poured the coffee into two mugs and set them on the table. He sat down, picking up a book off of a pile that Rory had left for him to read.

"Now that," Rory said a minute later, reentering the room, "is a great book. The best part is that they don't sugarcoat _anything_. They just tell it like it is, and it doesn't even make you depressed, just that you want to do something to make up for what happened to these people."

"Sounds truly inspirational," Jess replied in a mocking tone - but Rory knew he meant it. "Who called?" He put the book back on the stack and took a sip of his coffee. He had honestly never been a big fan of coffee, but Rory loved it so much that for some reason he always had a craving for it when she was drinking it.

"Oh, yeah. That was my mom." Rory slid her index finger along the rim of her mug. "She's not going to be able to make it home tonight, so I was actually wondering if I could stay here."

Jess shrugged. "No problem."

"Great. Thanks. I'll call her back right now."

As Rory phoned Lorelai, Jess poured their remaining coffee into two travel mugs. Grabbing Rory's coat off of the couch and his off of his bed, he handed it to her as soon as she had shut the phone.

Taking it, she smiled and said, "Walk?"

"You know me too well." Jess smirked and put his own coat on.

As they headed out the door, she asked, "Where to?"

"Out," he replied, teasing her with the word he told Luke much too often.

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"Ah, it's truly ten o'clock in Stars Hollow," Rory mused aloud.

"Hmm… Doose's is all closed up… their burglar alarm is flashing… the Twenty-Four Hour Mini-Mart is completely dark… yup. It's definitely ten o'clock in Stars Hollow." Jess looked up. "Oh, and of course the traffic light has been turned off."

Rory's head snapped up. "What? They don't turn off traffic lights at night! Isn't that the point of a traffic light - it stays on all the time and no one has to monitor it or turn it on or off? And - "

"Rory." Jess cut her off.

She looked at him, her eyes containing the sparkle they got when she was in the middle of a rant. "What?"

"I was kidding."

"Jess! That's not funny! You know I'm gullible - that's entirely unfair!" She pushed him away from her.

"Hey! Let's not get violent here, miss." Jess grinned his lopsided grin, and then a small laugh escaped his lips.

Rory rolled her eyes. "Of course, _you_ think this is hilarious, to make me look ridiculous in front of… well, no one but you, but that's not the point."

"You have to admit, it was kind of funny."

"It was so _not_."

"Fine."

They walked for a few moments in silence, until she looked over at him. "Alright, it was _kind_ of funny. But only a little."

"I knew you'd come around."

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They had been walking aimlessly for perhaps half an hour, sipping their coffee and discussing recent books and music, until Rory saw something lying on the floor of the gazebo.

"Hey… what is that?" she asked, tapping Jess to get him to turn and look.

They walked closer in order to see it better.

"That's Kirk's beloved 'Insectisyde' hat!" Rory exclaimed, kneeling down to pick it up.

"Careful," Jess warned, "he's probably hiding in a bush nearby, waiting to attack whoever picks it up."

"I think Kirk has a nine o'clock curfew," Rory giggled.

Taking the hat from Rory to examine it, Jess asked, "Has anyone ever figured out what 'Insectisyde' really means? I'm guessing that most of the town has figured by now out that it's actually not Mariah Carey's middle name."

"Jeez, I hope they know that by now. If not, they're much more dense than even we thought."

Just then Jess turned to Rory with a look that she knew all too well.

"What?" she asked.

"'What' what?" he returned her question innocently.

"Like I don't know you're scheming, Jess. But, lucky for you, I want in. And I'll have you know that if you don't include me, I'll go tell Kirk right now that you stole his treasured hat. And remember that Kirk in his white bunny pajamas with the matching pair of slippers and robe is _not_ a nice sight."

"Thanks for that. Now I'm going to have that _wonderful_ image in my mind for the next two months. You're a great friend, Ror. Really."

Rory tapped her foot on the wooden floor of the gazebo impatiently. "And you're great at being evasive. Really. Now, spill. What's going on in your rebellious mind?"

"Well…"

----------------

"I can't _believe_ we just did that!" Rory was running while buckled over with laughter, clutching Jess's hand just to stay standing.

"Jeez, it wasn't _that_ big of a deal."

"Maybe not for someone who does stuff like this all the time, I'll hand that to you."

They stopped running when they reached the front door of Luke's. Turning around, they admired their handiwork.

From the very top of the flagpole outside of Miss Patty's hung Kirk's 'Insectisyde' hat. It flapped in the wind ever so slightly.

"That's where it belongs," Jess said.

"Well, it certainly is much more flattering up there than on Kirk's head," Rory agreed. "Let's go in. It's getting late."

----------------

"Can I ask you something?" They were sitting on the couch, the end credits of _Footloose_ scrolling on the television screen. Rory was wearing a pair of Jess's sweats and wrapped in a fleece blanket.

"Shoot." Jess was a little wary of the serious tone in her voice, but he told himself not to read too much into it.

Rory turned so she was facing Jess. It was the question that had been lingering at the back of her mind all night. She had avoided asking it until now, but she knew that it would have to be asked sometime. "Why did you invite Dean to my party?"

Jess ran a hand through his hair. He knew that it was inevitable for her to ask at some point or another - he had just been avoiding it for as long as possible.

"I… I guess I just felt bad for giving you a hard time about him, and getting into that fight with him." He looked up to meet Rory's eyes. "And you like him, and it was your party, and I wanted you to be happy, and…"

"I've told you a million times Jess, I _don't_ like him." Rory pulled her knees up to her chest and wrapped her arms around them.

She was the worst liar he had ever met. But Jess knew better than to push the matter. "Fine. Well, he likes you, at least."

Rory looked up, and the glint in her eye gave away her hopefulness. "Really?"

Jess felt a pang of… something, although what it was he had no idea. Almost… sorrow? No, that couldn't be it. Why would he? Rory liked Dean, it was obvious, but Jess had always wanted the best for her. It's not like he imagined them as being best friends forever and Rory never having a boyfriend. He didn't. Really.

So he pushed all of that aside and replied, "Yeah. Definitely."

But for some reason, it felt like the wide grin that spread across her face was stabbing him in the chest.

----------------

The next morning, Rory was woken up by Jess shoving her (rather rudely, she thought).

"Rory. Wake up. He's in the diner."

"What? Who's in the diner?" Rory asked groggily, stifling a large yawn.

"Kirk!" Jess was whispering as though he was afraid Kirk had superhuman hearing and could hear them through the ceiling and walls of the diner.

Rory shot up to a sitting position, now fully awake. "No way! Has he noticed that his hat is missing yet?"

"Oh yeah." A smirk spread across Jess's face. "He's about to start his hunt to interrogate every single person in town. Actually, he has probably already cornered Caesar and forced him to fill out the one hundred and twenty-two question form he's printed out."

Rory hopped out of bed and was already on her way downstairs. "Come on, I want to go see!"


	4. Not Indefinitely Postponed

**author's note.** Once again, thanks so much to everyone who reviewed… although - not to complain or anything - I noticed that I got twice as many on the each of the first two chapters than Chapter 3…

Let me know if Jess seems too OOC. I tried my hardest.

Sorry for the lack of… anything in this chapter. Don't worry, things will start to heat up soon. I _promise_, I will not fall into the 4-5-6 chapter slump. Stick with me, please.

I've also posted another oneshot, called _What I Want._ It would be great if you would take a look.

**disclaimer.** Maybe, the world will grow feet and start tap dancing. Until that happens, I own only my ideas.

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**Chapter 4: Not Indefinitely Postponed**

---------------

_In the middle of every difficulty lies opportunity._

**- Albert Einstein**

---------------

Jess had always known that at one point or another, this time would come. The time that felt like he had been dreading his entire life. It felt similar to how he imagined someone who had to give an oral presentation in front of a large group and was scared sick to do it would feel. Jess, who prided himself in always being able to keep calm in any situation, had never been faced with this particular dilemma, but he imagined that it would go something like this. You would spend the weeks facing up to the event worrying and dreaming up all the absolute worst-case scenarios. Once the day of the event finally dawned, your stomach would feel like it was about to fall out. Upon arriving at the location your presentation was to take place, you would pray and pray and pray that for some - _any_ - reason, that it would be indefinitely postponed.

However, Jess figured that this rarely ever occurred. He also figured that your best friend would get a boyfriend eventually, too, although he still taking the worrisome presenter's approach: hoping that it would somehow be cancelled.

Unfortunately - but not _really_ much to his surprise - the day of his presentation arrived on a cold, dreary Saturday afternoon, and it wasn't cancelled, or even postponed.

"Hey," Rory greeted him with a grin, sliding onto a stool and flopping her bag down on the counter.

"Hey. Why are you so happy?" he asked, although he already knew the answer.

"Oh… nothing, really," Rory replied, smiling even more broadly, "Dean just asked me out to coffee, that's all."

"Really?" Jess said, feigning interest. "That's exciting and all, but didn't he already ask you out to coffee? You know, before your party?"

"Well, yeah, but then he never called because of the party, and so even though we agreed to do it sometime, we never set a date, so it was kind of still up in the air." She sipped at the coffee he set down in front of her.

"So… he really just set a date for when you two are going out to coffee - he didn't really just ask you out for coffee," Jess clarified, mad at himself for not being able to let it go. But it wasn't that easy.

Rory shrugged. "I guess."

He felt like he should make up for his rudeness - after all, at least she had told him. "Anyway, that's great. Have fun." He offered her a small smile before picking up his pad and pen. "I have some orders to fill, so I'll see you in a bit."

---------------

"Mom!" Rory called, throwing her bag onto the desk by the door and kicking her shoes off. "Mom, I need help!"

Moments later, Lorelai hurried down the stairs, a purse clenched in her teeth and attempting to fasten a necklace around her neck. After spitting the purse onto the kitchen table, and successfully clasping the necklace, she asked, "Wardrobe issues?"

Rory nodded. "I just have no idea. I mean, it shouldn't be that big of a deal. It's just coffee, right? Jeez… I'm being so… _girly_. Worrying what to wear, and how to act, and being completely not me, and - "

"Honey," Lorelai cut her off, "you're excited. It's normal."

Rory smiled and hugged her. "Thanks."

"Anytime. Now, what are our options here?" Lorelai strode over to the closet and began sorting through clothes, throwing possibilities onto Rory's bed.

"I was kind of thinking either the pink or the blue sweater, but I can't decide which one." Rory held up each choice on either side of her, examining her reflection in the mirror. "Jess always teases me when I wear the pink one, saying - " She stopped short and dropped the sweaters back onto her bed. "I guess I should be talking about Jess right now, huh?"

Lorelai sighed and was silent. "I guess not," she finally conceded.

"It's just so weird, you know? He's my best friend, and it's totally normal for people to want to talk about their best friend, only he's a guy… and now I'm going on a date with another guy. I don't want Dean to get the wrong idea."

"Honey, I think the only thing to do is to make things clear to Dean. People in this town have very twisted, sick minds, and they will try to corrupt him if you don't get to him first." Lorelai smiled at Rory. "Have you… have you tried talking to Jess about any of this?"

Rory shrugged. "I told him that I was going to coffee with Dean, if that's what you mean."

"And how did he act about that?"

"Fine. Why wouldn't he? I mean, he knew I was going to go on a date sometime. It's not anything that should bother him."

"Um… yeah. Of course."

---------------

Dean had suggested the coffee shop on the corner of Peach and Plum, and it seemed like the perfect place. Fairly quiet, it would be great to sit and talk in. Rory walked briskly, trying to contain the skip in her step. She didn't know why she was so giddy, exactly, but she had narrowed it down to two choices: either she really, really wanted coffee, or it was because this was the first time that any guy had shown interest in her - or that she had ever felt attracted to any guy, for that matter. Personally, she was betting it was the latter.

When Rory arrived, Dean was already there waiting for her. "Hey," he said, "I got us a table by the window."

Her stomach churned at the thought that he had waited for her… was she terribly late? Had she gotten the time wrong? As he ushered her over, she asked worriedly, "Am I late?"

He shook his head, smiling. "No. I just wanted to make sure we got a good table, that's all. I've heard it can get pretty busy here on afternoons."

"Well, you heard correctly," Rory replied, smiling in return, relief filling her. She sat down and ordered a coffee. "So, what's Chicago like?" she asked. "I've never been there."

---------------

Jess stood at the counter, rag in one hand, worn book in the other. He stared at the page, but he felt like he was reading in a foreign language. Slamming it shut, he looked down at the rag and realized that he had been cleaning the same spot on the counter for the past twenty minutes.

"Shit," he muttered, and, glancing around at the nearly empty state of the diner, called into the kitchen, "Luke, I'm going out!"

Ignoring the muffled response that Jess guessed was a negative one, he stuffed the book in his back pocket, grabbed his jacket off the hook, and hurried out the door.

Once on the street, he realized he had no idea where he was going. Usually when this occurred his feet took him to the bridge, but he couldn't go there today. That had become too much of _their_ spot, and thinking of Rory was the last thing he wanted to do right now.

Not when she was off with that jerk, that idiot. Why couldn't she see that she was way too good for Dean? But she had stood up for him - put Dean _in front_ of Jess - ever since she first met Dean. She had accused Jess of attacking Dean the day of the fight, without so much as pretending to listen to Jess's story.

Looking around, Jess realized that his feet had taken him directly to the corner of Peach and Plum. Right in front of the coffee shop. There was Rory, grinning and laughing at something that asshole had said.

Shoving his hands into his pockets, he pulled out a cigarette and walked away.

---------------

I don't normally like to beg for these, but I am now. Please, please, _please_ drop me a line!

And I promise, the next chapter will involve much Rory/Jess (although not _that_ kind… yet), how Lorelai feels about Dean, and much more excitement!


	5. Naïve

Hey, everyone!!

**author's note. **Firstly:I am SO, SO sorry about the extremely delayed update. I know. It's ridiculously lame. I hope I haven't lost all of my readers!

Secondly: Thanks so much for all of your fabulous reviews! I'm sorry that I didn't get to reply to you – hopefully after this chapter I'll have time to.

Thirdly: I don't have time to edit this right now, so I apologize for any typos, etc. I just really want to get this posted now.

**disclaimer. **Yeah, yeah, don't own.

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Chapter 5: Naïve 

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"We cannot direct the wind, but we can adjust the sails."

**- Chinese saying**

---------------

Jess shoved his hands into the pockets of his well-worn leather jacket. This jacket held a lot of memories, he thought with a sardonic smirk. He had first bought it when he went to visit his father. He had been only fourteen then; naturally the jacket had been huge on him. But he was naïve then; naïve to pray that the jacket would eventually fit him (it was sheer, dumb luck that he did, in fact, grow into it, and that he hadn't yet grown out of it); naïve to believe that a trip to California would be simple; and most of all, naïve to believe that his father would recognize him; that his father would be a good, caring person; that his father would be everything that Jess had hoped for and more.

_Stupid_, Jess thought to himself. He had been a stupid, naïve boy. But he wasn't that naïve anymore. No, he wasn't naïve at all now.

Furrowing his brow against the chilly autumn winds, Jess watched as every breath he exhaled let out a small, barely visible puff before it was swept away in the wind. He stopped at the bottom of the porch steps, debating whether or not he wanted to go forward. He had come here in a much deliberated hast – that was, he had debated for many days about whether to take this path, and only this morning when Rory had told him once again about her date with Dean that was scheduled for later that day, had he finally, suddenly, thrown on his jacket and come over here.

Watching one more of his breaths, he slowly walked up the porch steps. He faltered only slightly as he raised his hand to knock on the door, but then he did, and it was done. He was taking this path, and he wasn't enough of wimp to back out now.

Jess had to wait for a minute before he heard a voice shout, "The door's open!" Most times he wouldn't have waited at all – he would have simply walked right in – but he felt that due to the nature of his visit, he should wait.

He entered quickly, not wanting to let any of the cold outside air inside the warm house, and heard the voice shout again, "Who is it?"

"It's me," he replied, and then corrected himself, "Jess."

"Rory's not here," Lorelai's voice came down the stairs once again, and then Lorelai herself came into view, meeting him in the small foyer.

"I know," Jess said, kicking his muddy shoes off, "I was actually… I was hoping to talk to you."

"Oh," Lorelai said, looking startled as she attempted to force an earring into her ear, "okay, then." She signaled for him to come in and sit on the couch.

He complied, and after she had apparently deemed that the earring was a lost cause and thrown it haphazardly on the end table at the bottom of the stairs, she joined him.

"I know we haven't always been on the best of terms," he started, forcing himself to meet her eyes. "But I was hoping that we could just forget that right now, and then when we're done you can go back to hating me and throwing me dirty looks. And please… don't tell Rory that I was here."

"Alright," Lorelai agreed, narrowing her eyes at him, "what's all this about, Jess?"

"It's about – and don't freak out on me yet – Rory. And… Dean."

"Jess," Lorelai began, giving him her pity face just as he knew she would, "I know that Rory having a boyfriend must be hard on you –"

"No," he interrupted, perhaps a little to forcefully, and she looked slightly taken aback, "it's not about Rory having a boyfriend. It's just that Dean… I just get a really bad feeling about Dean. I'm… I'm worried that he's going to hurt her, because…"

"'Because' what?" Lorelai prodded.

"Because of the fight we got into, and Dean was… never mind. It's not important."

"Are you sure?" Lorelai wasn't stupid; she could tell that there was something Jess was leaving out.

"Yeah." He shoved his hands back into his pockets.

"Alright." Lorelai sighed, running a hand through her hair. "Okay, as long as we're on terms of strict confidentiality – I get a weird feeling about Dean, too. But, you know, that's probably just because he's my daughter's first boyfriend, and so that kind of weirds me out – " Jess could tell that she was still trying to convince herself more than she was trying to convince him – "but if Rory really likes him, then we should just trust her, Jess. Because I know that we both know if we try to interfere, Rory'll just block us out. Besides, Rory won't be discouraged by us saying that he merely gives us a 'bad feeling.'"

Jess nodded, knowing that she was right. And having Rory block him out would be worse than having her date Dean. "Right. Thanks, Lorelai." He stood up and walked to the door, slipping his shoes on.

Lorelai followed him and leaned against the doorframe. "Anytime, Jess," she replied. Their eyes met for a split second, and for once in his life, Jess knew that they were seeing eye to eye on an issue.

Jess gave a small, brief smile, and as he opened the door and slipped outside, said, "Just keep an eye on her… for me."

Not waiting for Lorelai's reply, he quickly closed the door and hurried down the steps, once again steeling himself against the wind, which seemed to have gotten much more bitter during his brief time inside.

---------------

To Jess's great relief, when Rory and Lorelai came to the diner that night, Dean was not with them.

Shortly after their arrival, Luke and Lorelai had gotten into an argument over… well, Jess and Rory really had no idea what it was over. However, so intense was the nature of their argument that it allowed Rory and Jess to slip upstairs to the apartment completely unnoticed.

"You want a soda?" Jess asked.

"Of course," she replied, sprawling across the couch.

He pulled out one soda for her and one for himself, and, tossing one to her, he pushed her over so that he could have a seat on the ancient couch.

"Hey!" she protested, kicking him and lying down again, this time laying her legs over his. "Ha. Never deprive a Gilmore girl of a comfy couch."

Jess raised an eyebrow and took a sip of his soda. "That's for sure."

They sat together in silence for a few minutes, each occasionally sipping their drinks.

Finally, Rory broke the silence. "Are you okay?" she asked, and although it was a question they must have both asked each other hundreds of times over the years, it startled him.

"Um… yeah. I mean, why wouldn't I be?" It wasn't quite an outright lie; he _was_ perfectly fine other than the fact that his best friend was dating a complete jerk.

"Oh, I don't know. You've just seemed sort of… quiet recently," Rory responded, flicking a lock of chocolate hair out of her eyes and putting her empty soda can on the cluttered coffee table.

"Well, I haven't been on purpose. I'm fine." _Liar_, Jess scolded himself. But honestly, what was he supposed to say?

"It's about Dean, isn't it?"

If Jess had been startled before, now he was shocked. "Uh… no! No, of course not. Why would you say that?"

Rory simply rolled her eyes. "I'm not stupid, Jess. I've known you for my whole life. Did you seriously expect me not to realize that there's something going on with you, and not to figure out that it has something to do with Dean?"

"No, Rory, I –"

"Seriously, Jess. How come you always know what's wrong with me in a split second, but you think that I'll never figure out anything about you? Do you really think I'm that oblivious?"

"No! Jeez, Rory, no. I just… I guess I didn't want to bother you. I don't know, you're so happy with Dean and everything – I just didn't want you to have to worry about things that aren't even a big deal." That was partly the truth, Jess consoled himself, he wasn't flat out lying.

"But it obviously _is_ a big deal, if it's bothering you! And I want you to be able to talk to me about these things. We used to be able to – why can't we still do that?" Rory had sat up now. She moved her legs off of Jess's lap and folded them up underneath her, kneading a floppy pillow in her hands.

"We can't because it's about your boyfriend!" Jess exclaimed.

"And why can't we talk about him? You're my best friend – we _have_ to be able to talk about him. I _want_ to be able to talk about him." She ran a hand through her hair before throwing it up into a messy bun.

"Fine," Jess gave in, "let's talk about him, then."

Rory let her hair down again. "Fine. You start."

"No, you're the one who wants to do this so badly. You start."

Rory sighed. They were both so stubborn that conflict resolution had never been their strong point. "Okay… I just wish that you guys could be friends. I mean, you're both great guys, and I just… I hate having to avoid talking about one of you when I'm with the other. I wish things weren't so… tense."

"Fair enough," Jess said. "Alright… now, wait before you freak out when I say this. I get a bad – okay, I won't say bad – a funny feeling about Dean. I mean, I know you really like him and all – " he continued when she tried to interrupt, successfully cutting her off – "but that's just the way I feel. But if you do really like him, and you think he's great, then I'll try to get along better with him."

"Seriously?"

Jess nodded. "Seriously." She had looked so happy, how could he say no?

Leaning over, Rory wrapped her arms around him and gave him a quick kiss on the cheek. "Thank you," she whispered into his ear.

"Now, Rory, kissing me could qualifying as cheating on this boyfriend you like so much," Jess teased, raising one eyebrow.

"Oh, shut up," Rory replied, smacking him soundly on the head with a pillow.


End file.
